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Reactions of 5-oxo-1-phenylpyrrolidine-3-carbohydrazides with 1,4-naphthoquinone derivatives and the properties of the obtained products

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Abstract

N′-(4-Oxo-1,4-dihydronaphthalen-1-ylidene)-1-phenyl-5-oxopyrrolidine-3-carbohydrazides and N′-(3-methyl-4-oxo-1,4-dihydronaphthalen-1-ylidene)-1-phenyl-5-oxopyrrolidine-3-carbohydrazides were synthesized by reactions of 5-oxo-1-phenylpyrrolidine-3-carbohydrazides with 1,4-naphthoquinone or 2-methyl-1,4-naphthoquinone. The alkylated analogues of the above products were obtained using ethyl iodide. The interaction of 5-oxo-1-phenylpyrrolidine-3-carbohydrazides with 2,3-dichloro-1,4-naphthoquinone was followed by formation of N′-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-1-phenyl-5-oxopyrrolidine-3-carbohydrazides. All these compounds were characterized using 1H, 13C NMR, IR and mass spectra. Some of the new compounds were tested for the antimicrobial and antifungal activity.

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Acknowledgment

The financial support from the Research Council of Lithuania is gratefully acknowledged (Project TAP-53/2010).

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Authors and Affiliations

  1. Department of Organic Chemistry, Kaunas University of Technology, Radvilėnų pl. 19, 50254, Kaunas, Lithuania

    Rita Vaickelionienė & Vytautas Mickevičius

  2. Department of Bioorganic Compounds Chemistry, Vilnius University Institute of Biochemistry, Mokslininku st. 12, 08662, Vilnius, Lithuania

    Gema Mikulskienė

  3. Department of Technology of Biologically Active Substances, Pharmacy and Biotechnology, National University “Lviv Polytechnic”, S. Bandery street 12, Lviv, Ukraine

    Maryna Stasevych, Olena Komarovska-Porokhnyavets & Volodymyr Novikov

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  1. Rita Vaickelionienė
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  2. Vytautas Mickevičius
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Correspondence to Vytautas Mickevičius.

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Vaickelionienė, R., Mickevičius, V., Mikulskienė, G. et al. Reactions of 5-oxo-1-phenylpyrrolidine-3-carbohydrazides with 1,4-naphthoquinone derivatives and the properties of the obtained products. Res Chem Intermed 37, 1009–1027 (2011). https://doi.org/10.1007/s11164-011-0306-y

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